Hexahydroxydiphenic acid

Oxidatively coupled derivative of gallic acid
Hexahydroxydiphenic acid
Chemical structure of hexahydroxydiphenic acid
Names
Preferred IUPAC name
4,4′,5,5′,6,6′-Hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylic acid
Other names
HHDP
3,4,5,3′,4′,5′-Hexahydroxydiphenate
3,4,5,3′,4′,5′-Hexahydroxydiphenic acid
Identifiers
CAS Number
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8490515 ☒N
PubChem CID
  • 10315050
CompTox Dashboard (EPA)
  • DTXSID901029565 Edit this at Wikidata
InChI
  • InChI=1S/C14H10O10/c15-5-1-3(13(21)22)7(11(19)9(5)17)8-4(14(23)24)2-6(16)10(18)12(8)20/h1-2,15-20H,(H,21,22)(H,23,24) ☒N
    Key: MFTSECOLKFLUSD-UHFFFAOYSA-N ☒N
  • InChI=1/C14H10O10/c15-5-1-3(13(21)22)7(11(19)9(5)17)8-4(14(23)24)2-6(16)10(18)12(8)20/h1-2,15-20H,(H,21,22)(H,23,24)
    Key: MFTSECOLKFLUSD-UHFFFAOYAZ
  • O=C(O)c2cc(O)c(O)c(O)c2c1c(O)c(O)c(O)cc1C(=O)O
Properties
Chemical formula
 C14H10O10
Molar mass 338.224 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Hexahydroxydiphenic acid is an organic compound with the formula [(HO)3C6HCO2H]2. It is the oxidatively coupled derivative of gallic acid[2] It is a white solid, although samples are typically brown owing to oxidation.

Ellagic acid.

Hexahydroxydiphenic acid is a component of some ellagitannins,[3] such as casuarictin. Luteic acid is the monolactone and ellagic acid is the dilactone of hexahydroxydiphenic acid.

See also

  • Diphenic acid

References

  1. ^ "MetaCyc hexahydroxydiphenic acid". biocyc.org.
  2. ^ Haslam, E.; Cai, Y. (1994). "Plant polyphenols (vegetable tannins): Gallic acid metabolism". Natural Product Reports. 11 (1): 41–66. doi:10.1039/NP9941100041. PMID 15206456.
  3. ^ Feldman, Ken S.; Iyer, Malliga R.; Liu, Yanze (2003). "Ellagitannin Chemistry. Studies on the Stability and Reactivity of 2,4-HHDP-Containing Glucopyranose Systems". The Journal of Organic Chemistry. 68 (19): 7433–7438. doi:10.1021/jo034495x. PMID 12968897.
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Types of ellagitannins
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
  • Elaeocarpusin
  • Helioscopin B
  • Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A, B, C and D
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other
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